dGTP (CHEM003408)

Record Information
Version1.0
Creation Date2014-08-29 06:51:21 UTC
Update Date2026-05-14 17:30:15 UTC
Accession NumberCHEM003408
Identification
Common NamedGTP
ClassSmall Molecule
Description
Under normal physiologic conditions, deoxyguanosine (dGuo) undergoes phosphorolysis by purine nucleoside phosphorylase (PNP, EC 2.4.2.1, an enzyme involved in the recycling of nucleosides and deoxynucleosides in cellular remodeling). However, when PNP is inhibited, deoxycytidine kinase (dCK, EC 2.7.1.74) shunts unmetabolized dGuo into deoxyguanosine triphosphate (dGTP), which accumulates and blocks DNA synthesis. Deficiency of purine nucleoside phosphorylase results in defective T-cell immunity. A correlation between the degree of T cell inhibition and the level of dCK activity is observed. (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2'-Deoxyguanosine 5'-triphosphateChEBI
Deoxyguanosine 5'-triphosphateChEBI
Deoxyguanosine triphosphateChEBI
2'-Deoxyguanosine 5'-triphosphoric acidGenerator
Deoxyguanosine 5'-triphosphoric acidGenerator
Deoxyguanosine triphosphoric acidGenerator
2'-Deoxyguanosine triphosphateHMDB
Deoxy-GTPHMDB
Deoxyguanosine triphosphate, 3H-labeledHMDB
Chemical FormulaC10H16N5O13P3
Average Molecular Mass507.181 g/mol
Monoisotopic Mass506.996 g/mol
CAS Registry Number2564-35-4
IUPAC Name({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional NamedGTP
SMILESNC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1
InChI IdentifierInChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
InChI KeyHAAZLUGHYHWQIW-KVQBGUIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
Purine Nucleoside Phosphorylase DeficiencySMP00210 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.59 g/LALOGPS
logP-0.61ALOGPS
logP-3.2ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)0.33ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area274.58 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.73 m³·mol⁻¹ChemAxon
Polarizability39.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB02181
HMDB IDHMDB0001440
FooDB IDFDB022623
Phenol Explorer IDNot Available
KNApSAcK IDC00019346
BiGG ID34502
BioCyc IDDGTP
METLIN ID6248
PDB IDNot Available
Wikipedia LinkDeoxyguanosine triphosphate
Chemspider ID58613
ChEBI ID16497
PubChem Compound ID65103
Kegg Compound IDC00286
YMDB IDYMDB00744
ECMDB IDECMDB01440
References
Synthesis Reference

Carl W. Fuller, Mark McDougall, Shiv Kumar, “Derivatives of 7-deaza -2’-deoxyguanosine-5’-triphosphate, preparation and use thereof.” U.S. Patent US06906185, issued June 14, 2005.

MSDSLink
General References
1. Kicska GA, Long L, Horig H, Fairchild C, Tyler PC, Furneaux RH, Schramm VL, Kaufman HL: Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes. Proc Natl Acad Sci U S A. 2001 Apr 10;98(8):4593-8. Epub 2001 Apr 3.
2. Stoop JW, Zegers BJ, Hendrickx GF, van Heukelom LH, Staal GE, de Bree PK, Wadman SK, Ballieux RE: Purine nucleoside phosphorylase deficiency associated with selective cellular immunodeficiency. N Engl J Med. 1977 Mar 24;296(12):651-5.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11096070
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22844265
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7929110